Railway service in Brewster can be traced as far back as December 31, 1848 when the
New York and Harlem Railroad expanded their main line from
Croton Falls to
Dover Plains stations. Realizing that the NY&H was going to run through the Town of Southeast, Walter and James Brewster constructed passenger and freight stations in 1848, and donated the buildings to the railroad. By 1869 it also served as the terminus of a railroad named the
New York and Boston Railroad which eventually became the
New York and Putnam Railroad, and by 1881 it was also a terminus for the
Boston, Hartford and Erie Railroad which was eventually acquired by the
New York and New England Railroad. On March 7, 1913, the NY&P officially became the
Putnam Division trains of the
New York Central Railroad and Brewster served as the terminus of that line up until May 28, 1958 when passenger service was discontinued on the Putnam Division main line. After that point, there remained one
Harlem Division train which traveled up the
Lake Mahopac Branch to the Mahopac railroad station and continued over Putnam tracks and making stops on upper Putnam stations until arriving at Brewster station. This "around the horn" train lasted until April 2, 1959 when all passenger service on the Putnam Division was terminated. It was one of the stations on the Harlem Line to serve the
Berkshire Hills Express and other limited stop trains that went from New York City all the way to
Pittsfield, Massachusetts and
North Adams, Massachusetts in the
Berkshires. Such through trains were replaced by shuttle transfers in 1950. As with most of the Harlem Line, the merger of New York Central with
Pennsylvania Railroad in 1968 transformed the station into a
Penn Central Railroad station. Penn Central merged with the
New Haven Railroad and its affiliates in 1969 giving them control of all lines in the village. Penn Central's continuous financial despair throughout the 1970s forced them to turn over their commuter service to the
Metropolitan Transportation Authority which made it part of Metro-North in 1983. ==Station layout==